Acylamino-hydroxybenzene arsine oxides



Patented Mar. 29, 1927.

v UNITED STATES PATENT OFFICE.

LUDWIG BENDA, OF MAINKUR, NEAR IRANKJEOIRHF-ON-THIEl-IMZAIN', GERMANY, AS- SIGNOR TO I. G. FARBENINDUSTRIE AKTIENGESELLSCHAFT, OF FRANKFORT-ON- THE-MAIN, GERMANY, A CORPORATION OF GERMANY.

AcYLAMmo-HYnRoxYBnN znNn ARSINE oxrnns No Drawing. Application filed June 19, 1925, Serial No. 38,329, and in Germany July 3, 1924.

I have found that acylized aminohydroxybenzene arsonic acids can be transformed into the respective arsonious acids, or their anhydrides that is to say, the hydrates of 6 arsine oxides and the arsine oxides themselves, without saponification taking place on on sulfurous acid is passed into this brown colored solution until the lemon-yellow sediment formed is not added to any longer. This precipitate is decanted by suction, washed with dilute hydrochloric acid and dissolved in five litres water; after a while the new product is precipitated as a white powder. The latter is decanted by suction and washed with water. It is hardly soluble in water, dissolves only gradually in a sodium carbonate solution double normal (in contrast to the parent material), is sparingly soluble in dilute sodium acetate solution, readily soluble in dilute alkalies, also in hot normal hydrochloric acid; by an addition to the latter solution of an excess of concentrated hydrohloric acid a white precipitate is formed.

acid ten times normal are added. At 25-30 the color has turned to white.

, Example 2.3-acetylamino-et-hydroxybenzene-l-a'rsine oxide.

mrcocm To a solution of 250 gr. 3-ch1oro-4- hydroxy-5-acetylaminobenzenel a r s o n i c 1 acid, 150 gr. sodium acetate and 250 gr. sodium iodide in 3000 centrated hydrochloric severely cooling-from acid passed in in a gradual stream until the yellow precipitate which has formed is not added to any longer. This is decanted by suction, washed with dilute hydrochloric acid and the yellow product of reaction ground together with 3000 cc; water until It is then neutralized with sodium acetate and. decanted by suction. After washing with water the compound is obtained as a slightly yellow crystalline powder. It is sparingly soluble in water, dilute sodium acetatesol'ution (in contrast to the parent material), soluble in hot normal hydrochloric acid, readily'soluble in methyl and ethyl alcohol, sparingly so in ether, acetone and chloroform.

acid are added, while cc. water, 600 gr. con-1 outside, an sulfurous acid group by a ous acid is passed aminobenzene-l-arsine oxide.

c NHcoom :0 500 gr. 3-methyl-4-hydroxy-5-acet laminobenzene-l-arsonic acid to be obtaine from &- amino-2-a cetylamino-6-methyl-l-phenol by substituting for the amino group the arsonic diazotization reaction 1000 cc. sodium carbonate solution double normal and 250 sodium iodide are dissolved cold, then adding 2000 gr. ice and 600 gr. concentrated hydrochloric acid into which sulfurin a gradual stream while well cooling from the outside (tem erature not to exceed 10). The lemon-yel ow pre cipitate formed is decanted by suction and treated with water and acetate as in the 2 previous exam le. JThe new compound is of a yellow co vents behaves Example 3.

like the compound of eral acid solution in the presence of a catalyzer. a 2. As new substances acylamino-hydroxyor and in contact with solbenzene-arsine oxides, being white owders dissolving hardly in'water, gradua y in dilute alkalies and sparingly in dilute sodium acetate solution.

3. As new substances .acylamino-hydroxybenzene-arsine oxides, the constitution of which corresponds to the formula Y NHX,

50 where X. -acyl Yzhalogen or methyl, being white powders dissolving hardly in water, gradually in dilute alkalies.

4. As new substance 5- hloro--hydroxy- 3-acetylaminobenzene-arsine oxide of the formula c Nn-cocm Having now particularly described and ascertained the nature of my said invention ,and in what manner the same is to be performed, I declare, that what I claim is:

1. A process for the production of acylamino-hydroxybenzene arsine oxides by reducing acylamino-hydroxybenzene arsomc acids with sulturous acid in a strongly min- ,0 being a white powder dissolving hardly in water, gradually in dilute alkalies.

In witness whereof I have hereunto signed my name this fourth day of June 1925.

LUDWIG BENDA. 

